CA2704986C - Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique - Google Patents
Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique Download PDFInfo
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- CA2704986C CA2704986C CA2704986A CA2704986A CA2704986C CA 2704986 C CA2704986 C CA 2704986C CA 2704986 A CA2704986 A CA 2704986A CA 2704986 A CA2704986 A CA 2704986A CA 2704986 C CA2704986 C CA 2704986C
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- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 150000008040 ionic compounds Chemical class 0.000 title claims abstract description 36
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 35
- 239000003999 initiator Substances 0.000 title claims description 17
- 239000000981 basic dye Substances 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 116
- 125000002091 cationic group Chemical group 0.000 claims abstract description 59
- 238000006243 chemical reaction Methods 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 49
- 239000000178 monomer Substances 0.000 claims abstract description 44
- 230000008569 process Effects 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 20
- 238000004132 cross linking Methods 0.000 claims abstract description 13
- 150000003254 radicals Chemical class 0.000 claims description 155
- -1 organometallic cation Chemical class 0.000 claims description 136
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 133
- 150000001875 compounds Chemical class 0.000 claims description 100
- 239000002904 solvent Substances 0.000 claims description 80
- 150000001768 cations Chemical class 0.000 claims description 71
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000000129 anionic group Chemical group 0.000 claims description 39
- 239000002555 ionophore Substances 0.000 claims description 31
- 230000000236 ionophoric effect Effects 0.000 claims description 31
- 230000005855 radiation Effects 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 239000001301 oxygen Chemical group 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
- 239000011593 sulfur Chemical group 0.000 claims description 22
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 239000012429 reaction media Substances 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 14
- 150000002892 organic cations Chemical class 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 14
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 14
- 125000001425 triazolyl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 12
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims description 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 12
- 150000003568 thioethers Chemical class 0.000 claims description 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- 125000000909 amidinium group Chemical group 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000005626 carbonium group Chemical group 0.000 claims description 10
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 10
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 10
- 150000002466 imines Chemical class 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 9
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 claims description 9
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052698 phosphorus Chemical group 0.000 claims description 6
- 239000011574 phosphorus Chemical group 0.000 claims description 6
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 6
- 150000003624 transition metals Chemical class 0.000 claims description 6
- KEJOCWOXCDWNID-UHFFFAOYSA-N Nitrilooxonium Chemical compound [O+]#N KEJOCWOXCDWNID-UHFFFAOYSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 5
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical group C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims description 5
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 150000002540 isothiocyanates Chemical class 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000005499 phosphonyl group Chemical group 0.000 claims description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
- 229920000767 polyaniline Polymers 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 229920000128 polypyrrole Polymers 0.000 claims description 5
- 235000013772 propylene glycol Nutrition 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 229950000688 phenothiazine Drugs 0.000 claims description 4
- 239000003504 photosensitizing agent Substances 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 229960000834 vinyl ether Drugs 0.000 claims description 3
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 2
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000003321 amplification Effects 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 150000004292 cyclic ethers Chemical group 0.000 claims description 2
- 150000004294 cyclic thioethers Chemical group 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000003951 lactams Chemical class 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 238000003199 nucleic acid amplification method Methods 0.000 claims description 2
- 150000002918 oxazolines Chemical class 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 229920002120 photoresistant polymer Polymers 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 9
- 150000001491 aromatic compounds Chemical class 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 125000005370 alkoxysilyl group Chemical group 0.000 claims 4
- 150000005840 aryl radicals Chemical class 0.000 claims 4
- 150000004291 polyenes Chemical group 0.000 claims 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 4
- 241001120493 Arene Species 0.000 claims 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 3
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 claims 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 1
- 150000008378 aryl ethers Chemical class 0.000 claims 1
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 24
- 239000000975 dye Substances 0.000 abstract description 18
- 230000004048 modification Effects 0.000 abstract description 4
- 238000012986 modification Methods 0.000 abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 111
- 150000003839 salts Chemical class 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 55
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000003792 electrolyte Substances 0.000 description 33
- 238000001704 evaporation Methods 0.000 description 33
- 230000008020 evaporation Effects 0.000 description 33
- 238000001914 filtration Methods 0.000 description 32
- 229910003002 lithium salt Inorganic materials 0.000 description 31
- 159000000002 lithium salts Chemical class 0.000 description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
- 239000002244 precipitate Substances 0.000 description 29
- 229910052799 carbon Inorganic materials 0.000 description 28
- 238000001035 drying Methods 0.000 description 28
- 229910052744 lithium Inorganic materials 0.000 description 27
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 26
- 239000004020 conductor Substances 0.000 description 26
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 22
- 239000000463 material Substances 0.000 description 22
- 229910052700 potassium Inorganic materials 0.000 description 22
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 21
- 239000011591 potassium Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 20
- 229910052786 argon Inorganic materials 0.000 description 18
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 17
- 150000003325 scandium Chemical class 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 14
- 150000002825 nitriles Chemical group 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- 150000001450 anions Chemical class 0.000 description 13
- 239000010408 film Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 239000001103 potassium chloride Substances 0.000 description 12
- 235000011164 potassium chloride Nutrition 0.000 description 12
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- 239000012973 diazabicyclooctane Substances 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 239000011777 magnesium Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000002131 composite material Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000010494 dissociation reaction Methods 0.000 description 8
- 230000005593 dissociations Effects 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000000010 aprotic solvent Substances 0.000 description 7
- 239000000499 gel Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 229920006112 polar polymer Polymers 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
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Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2805188A CA2805188C (fr) | 1996-12-30 | 1997-12-30 | Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique |
CA2704986A CA2704986C (fr) | 1996-12-30 | 1997-12-30 | Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002194127A CA2194127A1 (fr) | 1996-12-30 | 1996-12-30 | Anions delocalises utiles en tant que solutes electrolytiques |
CA2,194,127 | 1997-03-05 | ||
CA002199231A CA2199231A1 (fr) | 1997-03-05 | 1997-03-05 | Nouveaux materiaux ioniques |
CA2,199,231 | 1997-03-05 | ||
CA2704986A CA2704986C (fr) | 1996-12-30 | 1997-12-30 | Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique |
CA2248242A CA2248242C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions derives du malononitrile, et leurs utilisations comme materiaux a conduction ionique |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA2248242A Division CA2248242C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions derives du malononitrile, et leurs utilisations comme materiaux a conduction ionique |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA2805188A Division CA2805188C (fr) | 1996-12-30 | 1997-12-30 | Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique |
Publications (2)
Publication Number | Publication Date |
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CA2704986A1 CA2704986A1 (fr) | 1998-07-09 |
CA2704986C true CA2704986C (fr) | 2013-04-09 |
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Family Applications (9)
Application Number | Title | Priority Date | Filing Date |
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CA2248303A Expired - Lifetime CA2248303C (fr) | 1996-12-30 | 1997-12-30 | Sels d'amides perfluores, et leurs utilisations comme materiaux a conduction ionique |
CA2704986A Expired - Lifetime CA2704986C (fr) | 1996-12-30 | 1997-12-30 | Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique |
CA002248304A Expired - Lifetime CA2248304C (fr) | 1996-12-30 | 1997-12-30 | Materiaux carbones modifies en surface |
CA2683826A Expired - Lifetime CA2683826C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions pentacycliques ou derives de tetrazapentalene, et leurs utilisations comme materiaux a conduction ionique |
CA2248244A Expired - Lifetime CA2248244C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions heterocycliques aromatiques, et leurs utilisations comme materiaux a conduction ionique |
CA002244979A Expired - Lifetime CA2244979C (fr) | 1996-12-30 | 1997-12-30 | Conducteurs protoniques sous forme liquide |
CA2805188A Expired - Lifetime CA2805188C (fr) | 1996-12-30 | 1997-12-30 | Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique |
CA2248242A Expired - Lifetime CA2248242C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions derives du malononitrile, et leurs utilisations comme materiaux a conduction ionique |
CA2248246A Expired - Lifetime CA2248246C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions pentacycliques ou derives de tetrazapentalene, et leurs utilisations comme materiaux a conduction ionique |
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Application Number | Title | Priority Date | Filing Date |
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CA2248303A Expired - Lifetime CA2248303C (fr) | 1996-12-30 | 1997-12-30 | Sels d'amides perfluores, et leurs utilisations comme materiaux a conduction ionique |
Family Applications After (7)
Application Number | Title | Priority Date | Filing Date |
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CA002248304A Expired - Lifetime CA2248304C (fr) | 1996-12-30 | 1997-12-30 | Materiaux carbones modifies en surface |
CA2683826A Expired - Lifetime CA2683826C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions pentacycliques ou derives de tetrazapentalene, et leurs utilisations comme materiaux a conduction ionique |
CA2248244A Expired - Lifetime CA2248244C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions heterocycliques aromatiques, et leurs utilisations comme materiaux a conduction ionique |
CA002244979A Expired - Lifetime CA2244979C (fr) | 1996-12-30 | 1997-12-30 | Conducteurs protoniques sous forme liquide |
CA2805188A Expired - Lifetime CA2805188C (fr) | 1996-12-30 | 1997-12-30 | Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique |
CA2248242A Expired - Lifetime CA2248242C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions derives du malononitrile, et leurs utilisations comme materiaux a conduction ionique |
CA2248246A Expired - Lifetime CA2248246C (fr) | 1996-12-30 | 1997-12-30 | Sels d'anions pentacycliques ou derives de tetrazapentalene, et leurs utilisations comme materiaux a conduction ionique |
Country Status (6)
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US (15) | US6120696A (ja) |
EP (9) | EP0850932B1 (ja) |
JP (14) | JP4823401B2 (ja) |
CA (9) | CA2248303C (ja) |
DE (6) | DE69739501D1 (ja) |
WO (6) | WO1998029389A1 (ja) |
Families Citing this family (318)
Publication number | Priority date | Publication date | Assignee | Title |
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US5962546A (en) * | 1996-03-26 | 1999-10-05 | 3M Innovative Properties Company | Cationically polymerizable compositions capable of being coated by electrostatic assistance |
EP0850932B1 (fr) * | 1996-12-30 | 2009-07-22 | Centre National De La Recherche Scientifique (Cnrs) | Sels d'anions hétérocycliques, et leurs utilisations comme matéreiaux à conductin ionique |
EP0968196B1 (fr) | 1997-07-25 | 2004-10-27 | Acep Inc. | Composes ioniques perfluorovinyliques et leur utilisation dans des materiaux conducteurs |
DE69841891D1 (de) | 1997-07-25 | 2010-10-21 | Inst Of Organic Chemistry | Verwendung von ionenischen Verbindungen mit einer delokalisierten anionischen Ladung als Katalysatoren |
CA2215849A1 (en) * | 1997-09-11 | 1999-03-11 | Christophe Michot | New solvent and electrolytic composition with high conductivity and wide stability range |
DE69829955T2 (de) * | 1997-12-01 | 2006-03-02 | Acep Inc., Montreal | Salze von perfluorierten sulfonen und ihre verwendung als ionisch leitfähige materialien |
GB9726008D0 (en) * | 1997-12-10 | 1998-02-04 | Secr Defence | Eletrolyte |
EP1060200B1 (en) | 1998-03-03 | 2003-01-15 | E.I. Du Pont De Nemours And Company | Substantially fluorinated ionomers |
US6063522A (en) * | 1998-03-24 | 2000-05-16 | 3M Innovative Properties Company | Electrolytes containing mixed fluorochemical/hydrocarbon imide and methide salts |
FR2781932B1 (fr) * | 1998-07-10 | 2000-09-01 | Giat Ind Sa | Electrolyte solide polymere et ses procedes de preparation |
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